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I think GoD would be a VERY popular expansion to continue past POP - no need for custom content. GoD needs a little tweaking - but the foundation is there. after GoD - do OOW. There should be ample time for the players to progress from Classic-POP to finish off GoD and do a good chunk of OOW. Yes - the fights on OOW mobs won't be the same as there's not scripts - but you can always just make it tank and spank. You can get a good 1.5-2years out of this server no problem.
Like you reitterated - most the tweaking from Classic-POP would be pretty easy - GoD will take a little work and then OOW possibly - but there should be at least 1-2 months per expansion if done correctly with small group raiding. Solo servers go way faster - but small group raiding would take longer to progress due to flagging and gearing.
I think it'd be worth the time - but I'm not a dev. I wish I was and knew coding and I'd do my own - I've tried a few times.
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